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June 24, 2025 46 mins

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From Toxic Job to Dream Career: Jess Lindgren's Entrepreneurial Journey

In episode 111 of The Undiscovered Entrepreneur podcast, host Skooby chats with Jess Lindgren, a seasoned freelance personal and executive assistant with over 20 years of experience. Jess shares her inspiring journey of escaping a soul-crushing corporate job to support entrepreneurs like Pat Flynn of Smart Passive Income. The episode delves into pivotal moments such as Jess's strategic email that led to a 12-year career, the shift from fear of failure to fear of success, and how crucial it is to start small but start today. Jess also gives valuable advice for aspiring entrepreneurs and discusses the importance of maintaining authenticity and consistent effort in business. Tune in to hear Jess's insights and learn from her incredible entrepreneurial adventure.

Episode 106 

Entrepreneurial Wisdom: Pat Flynn's Strategies as Lean Learning Author and SPI Podcast Host



00:00 Introduction and Announcements
01:46 Special Guest Introduction: Jess
02:26 Jess's Entrepreneurial Journey
04:40 Transition from Corporate to Freelance
07:23 The Power of Networking and Email
10:41 Challenges and Insights in Entrepreneurship
21:40 The Importance of Openness in Parenting
22:09 Exploring the Fear of Success
22:30 Working with Pat: A Unique Experience
22:58 The Challenges of Social Media and Public Recognition
25:38 The Value of Being Behind the Scenes
28:07 Overcoming Career Pitfalls
34:33 Advice for Aspiring Entrepreneurs
37:53 Future Plans and Final Thoughts

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